Triethylamine → HCID 23045638, compound

HRID 2295757Notes

Reaction equation

HRID 2295757 reaction equation
[C:1]([Cl:6])(=[O:5])[CH2:2][CH2:3][CH3:4].COC1C=[C:11]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1.[CH2:21](N(CC)CC)[CH3:22].[Cl-].[CH2:29]([NH+](CC)CC)C>C1(C)C=CC=CC=1>[ClH:6].[CH2:11]([N:15]1[CH2:16][CH2:17][CH2:18][CH:19]([C:3]2[CH:4]=[CH:22][CH:21]=[C:1]([O:5][CH3:29])[CH:2]=2)[CH2:20]1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 6057251-(3-Methoxyphenyl)piperidineHCID 12698378Triethylazanium chloride

Product 1

HCID 23045638HCID 23045638, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Butyryl chloride (2.0 g, 0.019 mol) in dry toluene (5 ml) was slowly added to a solution of 3-methoxyphenylpiperidine (2.45 g, 0.013 mol) and triethylamine (1.92 g, 0.013 mol) in dry toluene at 5°. The mixture was stirred at room temperature for 30 min., whereupon the triethylammonium chloride formed was filtered off and the solvent evaporated. The crude N-butyryl-3-(3-methoxyphenyl)piperidine (2.82 g) dissolved in dry tetrahydrofuran (30 ml) was added to a suspension of LiAlH4 (2.0 g) in dry tetrahydrofuran (30 ml) under nitrogen. After reflux for 3 h in the mixture was hydrolysed, the precipitate filtered off and the solvent evaporated. The residue dissolved in light petroleum was passed through an alumina column. (Alternatively the residue could be distilled in vacuo). The product was precipitated as the hydrochloride and recrystallized from ethanol/ether yielding the pure product (3.6 g, 88%) mp 130°-1° C.

Workup

  1. customformed
  2. filtrationwas filtered off
  3. customthe solvent evaporated
  4. dissolutionThe crude N-butyryl-3-(3-methoxyphenyl)piperidine (2.82 g) dissolved in dry tetrahydrofuran (30 ml)
  5. additionwas added to a suspension of LiAlH4 (2.0 g) in dry tetrahydrofuran (30 ml) under nitrogen
  6. temperatureAfter reflux for 3 h in the mixture
  7. filtrationthe precipitate filtered off
  8. customthe solvent evaporated
  9. dissolutionThe residue dissolved in light petroleum
  10. distillation(Alternatively the residue could be distilled in vacuo)
  11. customThe product was precipitated as the hydrochloride
  12. customrecrystallized from ethanol/ether yielding the pure product (3.6 g, 88%) mp 130°-1° C.

Sources & evidence

ORD record
ord-448206b5e4854c4a8c7b9d0aac5314f6
Source dataset
uspto-grants-1984_01
Patent number
US04426386

Reaction notes

Loading…